Artificially sweetened beverages and mixes thereof



United States Patent 3,510,310 ARTIFICIALLY SWEETENED BEVERAGES AND MIXES THEREOF Robert G. Breckwoldt, Middletown, N.Y., assignor, by

mesne assignments, to The Pillsbury Company, Minneapolis, Minn., a corporation of Delaware No Drawing. Filed Feb. 11, 1966, Ser. No. 526,719

Int. Cl. A23] 1/00 US. Cl. 99-28 18 Claims ABSTRACT OF THE DISCLOSURE Presweetened beverage mix consisting essentially of N-cyclohexylsulfamic acid, an edible water-soluble amino carboxylic acid, an edible water-soluble organic acidulent. The mix is reconstituted to provide a beverage having texture and mouthfeel similar to a beverage sweetened with sugar.

This invention relates to low calorie dietetic food composition. More particularly, the present invention relates to food compositions containing an amino carboxylic acid and cyclohexylsulfamic acid.

It is an object of the present invention to provide a synthetically sweetened beverage mix which upon the addition of an aqueous medium closely assimilates sugar in respect to mouthfeel and texture.

Another object of the present invention is to provide a tart-tasting, synthetically sweetened beverage which assimilates sugar-sweetened beverages.

A further object of the invention is to provide a dry beverage mix which upon the addition of an aqueous medium substantially eliminates the aftertaste of artificially sweetened beverages.

Artifically sweetened beverages possess several adverse concomitant properties which limitthe use thereof as a An edible water-soluble amino carboxylic acid 5-25 N-cyclohexylsulfamic acid 1-4, An edible water-soluble organic acidulent 1--5 wherein the ratio of amino carboxylic acidto N-cyclo hexylsulfamic acid ranges from at least 1:1 to about 25:1.

The edible water-soluble amino carboxylic acids employed in the present invention mixes are those edible amino carboxylic acids that exhibit 'a solubility of at least five grams in one liter of water at 20 C. Exemplary organic amino carboxylic acids include those edible acids wherein the amino and carboxylic acid groups are linked via a saturated aliphatic hydrocarbon group. Illustrative amino carboxylic acids include those Water-soluble, edible amino carboxylic acids represented by the general for: mula:

wherein R is a monovalent group selected from the group consisting of lower alkyl (e.g., 1-5 carbon atoms), cycloaliphatic (e.g., 4-8 carbon atoms) and hydrogen, R and R are monovalent groups selected from the r. ICC

group consisting of hydrogen, lower alkyl and cycloaliphatic and X is an integer of a value ranging from 1 to 6. Typical edible amino carboxylic acids include glycine, alanine, valine, N-ethyl glycine, N-butyl glycine, N- cyclohexyl glycine, Isovaline, l-aminoisobutanoic acid, 2- aminobutanoic acid, 3-aminobutanoic acid, 4-aminobutanoic acid, 4-(N-methylamino) butanoic acid, 2- aminohexanoic acid, Lysine, methionine, mixtures thereof and the like. Exceptional results are obtained wherein the edible amino carboxylic acid is glycine.

, Edible water-soluble organic acidulents adaptable to the dry mixes include the mono and polycarboxylic organic acids such as adipic, citric, fumaric, malic, lactic, tartaric and succinic acids and mixtures thereof. Also adaptable are the cold water-soluble fumaric and adipic acids which generally include an additional surfactant to en hance the solublility thereof such as disclosed in US. Patents, 3,151,986 by J. H. Van Ness; 3,152,909 by S. P. Rafiensperger et al.; 3,016,299 and 3,016,300 by S. P. Ratfensperger et al. and 3,181,953 by J. H. Van Ness et al.; 3,169,872 by R. L. Rau et a1. Superior results are achieved via the use of unmodified adipic acid in combination with N-cyclohexylsulfamic acid and the organic amino carboxylic acid, particularly glycine, in the amounts hereinbefore stated.

In a preferred embodiment of the present invention, there is provided dry beverage mixes and beverages containing about 10 parts 'by weight of an edible amino carboxylic acid, about 1 to about 4 parts by weight N- cyclohe'xylsulfamic acid and from about 1 to about 5 parts by weight of an organic acid acidulent.

In a more limited aspect of the present invention, there is provided beverages and beverage mixes containing in addition to the aforementioned acids, an edible watersoluble viscosity agent in an amount sufiicient to provide an aqueous medium with a viscosity greater than that of water (e.g., greater than 1.005 centipoises at 20 C.) Illustrative water-soluble viscosity agents are the hydrocolloids that provide a hydrocolloid solution having a viscosity greater than water when 0.25 gram of the hydrocolloid are dispersed in ml. of Water at 20 C. Typical viscosity agents include sodium carboxymethylcellulose, sodium alginate, gum arable, gum karaga, guar gum, okra gum, carrageenin, methylcellulose, ethylcellulose,

sodium carrageenate, hydrolyzed collagen, dehydrated gelation, gelatinized starch, polyvinylpyrolidene, mixturesthereof and the like. The amount of water-soluble viscosity agent added to the beverage mix generally ranges from about 0.4 to about 2 parts by weight per 10 parts by weight of edible amino carboxylic acid and preferably ranges from about 0.75 to about 1.5 parts by weight per 10 parts by weight of edible amino carboxylic acid. The preferred hydrocolloid is sodium carboxymethylcellulose.

The instant dry mixes may be prepared by a variety of means such as dry blending of the ingredients, spray drying,.agglomeration, drum drying and other conventional means of providing a dry mix of uniform consistency.

Various flavoring agents, clouding agents, dyes, preservatives, antioxidents, buffering agents, nutritional additives (e.g., vitamins) and the like conventionally added to dry beverage mixes and beverages are adaptable herein.

Beverages may also be prepared by directly admixing the beverage mix ingredients separately or any combination thereof into water followed by agitation thus pro viding a beverage. In general, the amount of water and mix should be sufficient to provide a suitable beverage. Typical employable amounts range from about 1 to about 4 parts by weight of N-cyclohexylsulfamic acid to about 1,000 parts by weight of water and preferably about 1,000 parts by weight of water to about 1 to about 3 parts by weight of N-cyclohexylsulfamic acid.

7 The following examples are illustrative of the invention:

EXAMPLE I Orange drink EXAMPLE II Pineapple-grapefruit drink A pineapple-grapefruit drink was prepared from the An orange drink was prepared from the following infollowing ingredients and proportions thereof: gredients and proportions thereof: Ingredients: Grams lngregllenis: Grams Glycine 100 Ycme Cyclamic acid y y acld Adipic acid 35 Citric id 30 Sodium carboxymethylcellulose 8 Sodlum cajrboxymetglylcenulose 8 clouding agent 1 30 y clpudmg agent 0.8 Flavoring -2 6 Flavoring agent4 12 Dye 0,27 Dye 3 37% hydrogenated vegetable oil and 5% glyceryl abletate C1 (1 base sold b Beatrice Foods Co. contain 11 about 50% 3; weight hydr vegetable Oil 011 slim? arabic r hi i t ii ri fli ligiiiiiie-om efmit Juice Flavor sold by P0- l iii itation Orange Juice Flavor sold by Polaks Frutal L E f Qfi contammg about 25% flavor on on Works, Inc. containing about 25% flavor oil on a gum carrier.

In preparing the artificially sweetened orange drink In preparing the artificially sweetened pineappleall the ingiedients except the flavor were dry blended in grapefruit drink, all the ingredients except the flavor a ball mill. The flavor was then added to the aforemenwere dry blended in a ball mill. The flavor was then tioned dry blend followed by additional dry blending for added to the aforementioned dry blend followed by addia period of time sufiicient to provide an admixture theretional dry blending for a period of time sufficient to proof. The admixture was then added to 10 quarts of water, followed b stirrin or shakin for -60 seconds For vlde an admlxture thereof A dunk was prepared by com arativg u osges a d (Earl 8 mix containin' the adding to the admixture 10 quarts of water followed by follogvin in Quins thereof mechanical stirring for a suflicient period of time to d thegaforementionelzi gocedure P effect homogenous dispersion of the drink mix therein pare y P 30 (about 30 seconds). The resultant drink possessed su- Ingredients: Grams perior mouthfeel and texture. Sweetness level was en- Sugar 750 hanced by the combination of cyclohexylsulfamic acid, Adipic acid glycine and citric acid without a concomitant off-taste. Sodium carboxymethylcellulose 8 In a similar manner, tart-tasting artificially sweetened Clouding agent 30 35 beverage mixes may be prepared by employing other Flavoring agent 6 edible organic acidulents or mixtures thereof such as Dye 0.27 fumaric, malic, lactic, tartaric and succinic acids. Calcium cyclamate 10.15 Saccharin calcium 0.85 EXAMPLE III Adipic acid 35 I Sodium carboxymethylceuulose g In order to ascertain the effect of the organic acidulent, clouding agent 1 30 the following drink mixes and resultant beverages in the Flavoring agent 2 6 gram amounts listed in Table I, according to the method Dye 7 of Example I, were prepared. 1 S E 1 I f f t t 1 Beverages were prepared by adding 10 quarts of water a 232 1 3g gg flg fi to each of the batches below and compared by testing.

TABLE I Sodium Cyclohexylcarboxysulfamic Adipie nietliyl- Flavoring Glycine acid acid cellulose Cloud agent Dye RunI 100 12 35 s 30 6 0.27 Run II- 100 15 0. 0 s 30 0 0. 27 Run III 100 I 20 0.0 s 30 0 0.27 Run IV 100 30 0.0 s 30 6 0.27 Run v.-. 100 40 0. 0 s 30 0 0. 27 Run vI 100 0. o s 30 a 0. 27 Run VIL- 100 0.0 s so 0 0.27 Run viII 100 0. 0 s 30 0 0. 27 Run IX- so 50 0. 0 s 30 6 0. 27 Run X. 50 60 0. 0 8 30 6 0. 27 Run XL.-- 50 70 0. 0 s 30 6 0. 27

Upon testing the aforementioned orange drink, it was Run I produced a satisfactory orange drink similar in observed that the orange drink containing glycine and characteristics to that of Example I. Beverages from Runs N-cyclohexyl sulfamic acid was very similar to that con- 65 II-VIII did not contain the organic acidulent. However, taining sugar in respect to texture, taste and mouthfeel. the acidity thereof was supplied by increasing the amount The orange drink containing the calcium cyclamate and of cyclohexylsulfamic acid. Run H had extremely poor saccharin calcium was characterized by the lack of the taste and weak flavor. As the cyclohexylsulfamic acid texture, taste and mouthfeel characteristic when 'comwas increased in Runs III-VIII, flavor and sweetness was pared to the orange sugar-sweetened drink. Comparison increased as well as the olf-taste. It was also noted that as of panel preference tests between the aforementioned the level of cyclohexylsulfamic acid was increased in the orange drinks containing the calcium cyclomate with that beverage, the beverage developed an adverse cloying of the invention indicated a clear preference for the latsweet taste (i.e., lacking the tart taste typical of and necester. Addition of 100 grams of glycine to the drink consary for beverages). For comparative purposes, similar taining calcium cyclamate and saccharin calcium failed to tests were run by increasing the glycine level while holdprovide any benefits thereover.

ing the cyclohexylsulfamic acid constant in the absence of the adipic acid. It was Observed that low levels of glycine failed to provide the necessary sweetness and flavor thereof (e.g., Runs IX-XI). At increased levels of glycine, the beverage developed an adverse bland, cloying taste. Employment of inorganic acids (e.g., phosphoric acid) in amounts suflicient to provide a comparable acidity as a substitute for the organic carboxylic acids failed to provide an acceptable beverage.

EXAMPLE IV Orange drink An orange drink was prepared pursuant to dry mix procedure of Example I from the following ingredients Beatreme 1292B sold by Beatrice Foods Co. 2 See Example I for footnote 2.

The above ingredients were then mixed to provide one gallon of orange drink.

What is claimed is:

1. A beverage consisting essentially of the following ingredients in parts by weight:

Parts by weight Water 1000 Edible water-soluble amino carboxylic acid 5-25 N-cyclohexylsulfam-ic acid 1-4 Edible water-soluble organic acidulent 1-5 wherein the ratio of amino carboxylic acid to N-cyclohexylsulfamic acid ranges from at least 1:1 to about 25:1.

2. The beverage according to claim 1 wherein the edible amino carboxylic acid is an alpha-monoamino, monocarboxylic acid and the water-soluble acid is at least one member selected from the group consisting of adipic, fumaric, citric, malic, lactic, tartaric and succinic acid.

3. The beverage according to claim 2 wherein the amino carboxylic acid is glycine and the beverage contains from about 0.75 to about 1.5 parts by weight sodium carboxymethylcellulose for each parts by weight glycine therein.

4. A dry beverage mix consisting essentially of an admixture of the following ingredients in parts by weight:

at least one edible water-soluble amino carboxylic acid;

N-cyclohexylsulfamic acid; and

at least one edible water-soluble organic acidulent wherein the ratio of amino carboxylic acid to N- cyclohexylsulfamic acid ranges from at least greater than 1:1 to about 25:1 and the amount of ediable water-soluble organic acidulent therein ranges from about 1 to about 5 parts by weight for each 10 parts by weight of said amino carboxylic acid.

5. A dry beverage drink mix according to claim 4 wherein the amino carboxylic acid is at least one edible acid represented by the general formula:

wherein R is a member selected from the group consisting of lower alkyl, cycloaliphatic and hydrogen, R and R are members selected from the group consisting of hydrogen, lower alkyl and cycloaliphatic and X is an integer of a value ranging from 1 to 6.

6. The dry beverage mix according to claim 4 wherein COOH the edible amino carboxylic acid is an alpha-monoam-ino, monocarboxylic acid.

7. The dry beverage mix consisting essentially of the ingredients according to claim 6 wherein the water-soluble acid is at least one member selected from the group consisting of adipic, fumaric, citric, malic, lactic, tartaric and succinic acid.

8. The dry beverage mix according to claim 7 wherein the amount of edible amino carboxylic acid contained in the dry mix ranges from 5 to 15 parts by weight and the ratio of amino carboxylic acid to N-cyclohexylsulfamic acid ranges from at least greater than 1:1 to about 15: 1.

9. The dry beverage mix according to claim 7 wherein the amino carboxylic acid is glycine.

10. The dry beverage mix according to claim 9 wherein the organic acid is adipic acid.

11. The dry beverage mix according to claim 9 wherein the organic acid is citric acid.

12. The dry beverage mix according to claim 9 wherein the organic acid is fumaric acid.

13. The dry beverage mix according to claim 9 wherein the organic acid is malic acid.

14. The dry beverage mix according to claim 10 wherein the ingredients in parts by weight range fromabout 10 parts by weight glycin, from about 1 to about 3.5 parts by weight N-cyclohexylsulfamic acid and from about 1 to about 5 parts by weight adipic acid.

15. The dry beverage mix according to claim 10 wherein the ingredients in parts by weight range from about 10 parts of glycine, from about 1 to about 3.5 parts N-cyclohexylsulfamic acid and from about 1 to about 5 parts citric acid.

16. The dry beverage mix according to claim 11 wherein the ingredients in parts by weight range from about 10 parts glycine, from about 1 about 3.5 parts N-cyclohexylsulfamic acid and from about 1 to about 5 parts fumaric acid.

17. The dry beverage mix according to claim 13 wherein the ingredients in parts by weight range from about 10 parts by weight glycine, from about 1 to about 3.5 parts N-cyclohexylsulfamic acid and from about 1 to about 5 parts malic acid.

18. A dry beverage mix consisting essentially of an admixture of the following ingredients in parts by weight:

glycine;

sodium carboxymethylcellulose;

N-cyclohexylsulfamic acid; and

at least one water-soluble organic acidulent selected from the group consisting of adipic, fumaric, citric, malic, lactic, tartaric and succinic acid wherein the ratio of glycine to N-cyclohexylsulfamic acid ranges from at least greater than 1:1 to about 25:1, the amount of edible water-soluble organic acidulent therein ranges from about 1 to about 5 parts by weight for each 10 parts by weight of said glycine, and the amount of sodium carboxymethylcellulose therein ranges from about 0.75 to about 1.5 parts by weight for each 10 parts by weight of said glycine.

References Cited UNITED STATES PATENTS 2,876,107 3/1959 Jucaitis et al 99l41 3,023,106 2/1962 Common 9978 3,082,091 3/ 1963 Smith et a1. 9978 3,105,792 10/1963 White 16757 7 FOREIGN PATENTS 602,572 8/1960 Canada. 369,141 7/1958 Japan.

A. LOUIS MONACELL, Primary Examiner S. B. DAVIS, Assistant Examiner U.S. Cl. X.R. 9978, 141 

